Each year, Wripple’s Team Up Report takes the pulse of the state of the freelance economy, offering insight into how freelancers and the companies that hire them are navigating the evolving world of work. This year, our third annual study brought together the voices of 200 freelancers and 200 business leaders to provide insight on satisfaction levels, collaboration dynamics, future expectations, and the cultural shifts reshaping how we work together.

The freelance revolution is no longer emerging—it’s here, evolving, and challenging the traditional rules of how work gets done. That’s why this year’s report does two things:  

#1 Annual pulse on the freelance economy—overall satisfaction, working relationships, and expectations for the future.  ‍

#2 Trends standing out in 2025—areas that influence the freelance economy’s hiring practices, ways of working and cultural dynamics. These include:

• The transformative power of AI‍
• The stubbornness of traditional workplace norms‍
• The growing age divide in freelancer satisfaction and opportunity
• The importance—and complexity—of cultural fit‍
• A new focus on freelancer wellness and staying power

Together, these insights offer a picture of where the freelance economy stands today—and where it’s heading.

In the months ahead, we’ll be diving deeper into these emerging themes through a series of follow-up articles. We’ll explore the practical implications of these trends and offer guidance for both freelancers and companies looking to adapt.

For now, consider this your big-picture guide to the freelance landscape in 2025.

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Throughout this report, when we refer to freelancers, we mean independent professionals who are not hired as a traditional full-time employee. They could technically be a freelancer working on a project basis or a contractor on a long-term assignment. When we refer to companies, we mean Wripple clients who are full-time employees at organizations that hire freelancers.

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Annual Pulse on the Freelance Economy

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Satisfaction

Freelancers and Companies: Happily Working Together

High satisfaction levels were reported in 2024, and that continues to be the case in 2025. Overall satisfaction levels among freelancers and companies are at impressive levels, with 97% of both groups reporting that they are at least somewhat satisfied with their freelance partnerships. For freelancers, there was a noticeable bump in satisfaction this year.

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On the client side, while most are thrilled with the quality of work freelancers deliver, they’re struggling to find enough qualified talent when they need it.

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🔑 Key Takeaway: Satisfaction is strong, but as companies rely more on freelance talent, finding available freelancers is becoming just as important as managing the work itself.

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Working Together

Collaboration Is High—But So Are Blind Spots

Both groups agree on one thing: working together is mostly smooth sailing. But there's a wrinkle. Companies are significantly more likely to say that freelancers show respect for their time, perspectives, and priorities. Meanwhile, only 1 in 3 freelancers feel this same level of respect from the companies they’ve worked with in these areas.

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This mismatch isn’t new. In our 2024 Team Up Report, we saw a similar gap when companies gave themselves high marks for professionalism, while freelancers often felt that clients didn’t maintain standards and professionalism.

These disconnects may reveal something deeper about how freelancers are perceived, not as full contributors but as temporary help. And if we want to foster deeper collaboration, mutual respect and professionalism must be part of the deal.

🔑 Key Takeaway: Respect isn't just nice—it’s essential for high-functioning teams. Companies need to be intentional about supporting freelancer relationships.

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Future Expectations

Freelancing Isn’t a Stopgap—It’s the Goal

The "future of work" is becoming the “present of work,” especially for freelancers. Most plan to stay independent, while a significant number of side hustlers and part-timers are preparing to go all-in.

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Even more surprising is that over half of full-time employees at companies said they’d consider leaving their jobs to freelance full-time.

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Tracking along with this data is the fact that 84% of freelancers expect demand for their services to increase in the next two years. This is similar to our 2024 findings, where 82% expected the number of opportunities to increase.

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On the company side, 81% expect budgets for freelancers to grow, while 64% expect hiring to increase. The latter represents a decrease from 2024 but is higher than in 2023.

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This subtle but telling gap suggests a shift in strategy: companies may be investing more per freelancer, focusing on highly skilled or specialized talent over scaling volume.

🔑 Key Takeaway: Freelancing is here to stay, and it may soon get a major influx of new talent. Companies are prioritizing quality and specialization, while freelancers are leaning in for the long haul.

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Trends Standing Out in 2025

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Impact of AI

AI Is Everywhere—But Not Everyone Uses It the Same Way

AI is no longer optional—it’s part of the work. Nearly all freelancers and companies are using it, with younger freelancers more likely to dive deep.

Freelancers are using AI for speed and job prep. Companies are turning to AI for hiring—using digital footprints, automated interviews, and skill assessments to make decisions faster.

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But there’s a twist: smaller companies appear to be more likely to fully embrace AI than their larger peers. What we've heard from large enterprise clients is that they are risk averse. Policies either haven't been set, or the legal department has said not to use AI yet.

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🔑 Key Takeaway: AI is reshaping hiring and productivity. The companies and freelancers who lean in will have the edge.  

🔎 Looking ahead: Employers and freelancers must turn to AI to thrive in the future of work. Future articles will explore how both can adopt this powerful technology to realize massive benefits while limiting potential risks.

Changing Workplace Norms

The Push and Pull of Changing Norms

Flexibility. Diversity. Wellness. Both freelancers and companies say these workplace values matter—but there’s a gap between freelancers and companies. Many businesses say they’re committed to evolving norms, but freelancers are more skeptical.

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One especially stubborn barrier? Traditional hiring mindsets. Companies often pass over skilled freelancers who are “over-qualified” or can’t be onsite, even when their resumes shine and they are willing to do the work.

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🔑 Key Takeaway: Companies know change is necessary, but old habits die hard. Real transformation requires not just awareness, but bold, structural shifts in how talent is engaged.

🔎 Looking ahead: We’ll dive deeper into how flexible work models, skills-based hiring, and a focus on inclusion are reshaping the modern job market, even while traditional biases still linger. 

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The Age Divide

Experience Isn’t Always Rewarded

Beneath the high overall satisfaction scores lies a clear generational gap. Younger freelancers (under 45) are more than twice as likely to be very satisfied with their freelance experience compared to those 45 and older. Why the drop-off? Older freelancers report significantly lower satisfaction with both pay and the lack of meaningful opportunities. This points to a freelance economy that potentially values flexibility over experience.

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🔑 Key Takeaway: Age brings wisdom—and higher expectations for pay and professionalism—but seems to reduce opportunity. For the freelance economy to be truly inclusive, it must better support mid- and late-career professionals.  

🔎 Looking ahead: As freelancing goes mainstream, we’ll explore how that future looks different depending on your age and answer the question: Is experience a competitive advantage, or is the market skewed in favor of younger talent?

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Cultural Fit

Cultural Fit: A Hiring Hot Button

Nearly all companies factor in “cultural fit” when hiring, and many rate it as more important for freelancers than full-timers. That might sound counterintuitive—but for short-term projects, seamless integration matters.

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Yet how “fit” is defined varies. Some focus on work style and personality alignment. Others—especially larger firms—emphasize shared values. For freelancers, this means being able to read the room and adapt quickly while staying true to themselves.  

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🔑 Key Takeaway: “Cultural fit” is real—but it’s also subjective and could lead to sub-optimal decisions.  

🔎 Looking ahead: Future articles will explore how freelancers can navigate and succeed within different team cultures.

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Freelancer Wellness

Wellness, Learning, and the Freelance Life

Wellness isn't just a trend—it's a freelance survival skill. Freelancers are prioritizing sleep and healthy diets while also pushing themselves to grow.

More than half are intentionally pursuing stretch assignments and continuously upskilling. This reflects a freelance mindset focused on reinvention and resilience, not just gig-to-gig survival.

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🔑 Key Takeaway: Freelancers are optimizing both their health and their skill sets. Companies should see them as growth-minded partners—not just project-based doers.

🔎 Looking ahead: Future articles will look at what it truly means to succeed as a freelancer, from breaking into big-company work and upskilling to staying competitive to navigating AI, job satisfaction, and long-term financial and personal well-being.  

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A Flexible Future Constrained by Rigid Roots of the Past

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The undeniable benefits of the freelance economy—for both workers and companies—means it’s here to stay. However, traditional workplace practices and norms, and the disruptive force of AI, present challenges. Both sides of the talent equation are rethinking how work gets done and where their priorities lie—but progress is patchy. There’s enthusiasm and momentum, but also tension, structural bias, and generational disparities that need to be addressed before true transformation can take hold.

To succeed in 2025 and beyond, both sides need to rethink old assumptions and get ready to work differently—together.

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